Thermosetting resin composition, thermosetting resin sheet, electronic component, and electronic device

Abstract

Provided are: a thermosetting resin composition, for use in an organic material suited to high frequency use, that has outstanding low dielectric tangent, heat resistance, flexibility, and ease of workability; a thermosetting resin sheet; an electronic component; and an electronic device. The present invention is a thermosetting resin composition that includes the following constituents (A1)-(C). (A1) Polyimide resin: a polyimide resin including a diamine residue with formula (8) and/or formula (9) (in formula (8), a, b, c, and d are integers 1 or greater that meet the conditions a+b=6-17 and c+d=8-19, and the dashed lines denote carbon-carbon single bonds or carbon-carbon double bonds) (in formula (9), e, f, g, and h are integers 1 or greater that meet the conditions e+f=5-16 and g+h=8-19, and the dashed lines denote carbon-carbon single bonds or carbon-carbon double bonds). (B) Phenylene ether resin: a phenylene ether resin that has a number average molecular weight of 500-5,000 and, at a terminal of a molecular chain, includes at least one cross-linked functional group selected from the group consisting of a phenolic hydroxyl group, an acryl group, a vinyl group, and an epoxy group. (C) Maleimide resin: a maleimide resin.

1 . A thermosetting resin composition comprising the components of (A1), (B), and (C) specified below:
 polyimide resin (A1): a polyimide resin containing a diamine residue as represented by the formula (8) and/or the formula (9),   
       
         
           
           
               
               
           
         
         wherein in the formula (8), a, b, c, and d are each an integer number of 1 or higher and satisfy the relations of a+b=6 to 17, and c+d=8 to 19, and each broken line represents either a carbon-carbon single bond or a carbon-carbon double bond, 
       
       
         
           
           
               
               
           
         
         wherein in the formula (9), e, f, g, and h are each an integer number of 1 or higher and satisfy the relations of e+f=5 to 16, and g+h=8 to 19, and each broken line represents either a carbon-carbon single bond or a carbon-carbon double bond, 
         phenylene ether resin (B): a phenylene ether resin having a number average molecular weight of 500 or more and 5,000 or less and having at least one crosslinkable functional group selected from the group consisting of phenolic hydroxyl group, acryl group, vinyl group, and epoxy group located at a molecular chain end, and 
         maleimide resin (C): a maleimide resin. 
       
     
     
         2 . A thermosetting resin composition comprising the components of (A2), (B), and (C) specified below:
 polyimide resin (A2): a polyimide resin containing a diamine residue as represented by the formula (1),   
       
         
           
           
               
               
           
         
         wherein in the formula (1), m represents an integer number of 1 to 60; R 5  and R 6  may be identical to or different from each other and they each represent an alkylene group containing 1 to 30 carbon atoms or a phenylene group; and R 1  to R 4  may be identical to or different from each other and they each represent an alkyl group containing 1 to 30 carbon atoms, a phenyl group, or a phenoxy group, 
         phenylene ether resin (B): a phenylene ether resin having a number average molecular weight of 500 or more and 5,000 or less and having at least one crosslinkable functional group selected from the group consisting of phenolic hydroxyl group, acryl group, vinyl group, and epoxy group located at a molecular chain end, and 
         maleimide resin (C): a maleimide resin. 
       
     
     
         3 . A thermosetting resin composition as set forth in  claim 1 , wherein the polyimide resin is the polyimide resin (A1) and the polyimide resin (A2). 
     
     
         4 . A thermosetting resin composition as set forth in  claim 3 , wherein in the polyimide resin (A2), diamine residues represented by the formula (1) account for 20 to 80 mol % of all diamine residues, which account for 100 mol %, in the polyimide while at the same time, in the polyimide (A1), diamine residues represented by the formula (8) or formula (9) altogether account for 1 to 30 mol % of all diamine residues, which account for 100 mol %, in the polyimide, 
       
         
           
           
               
               
           
         
         wherein in the formula (1), m represents an integer number of 1 to 60; R 5  and R 6  may be identical to or different from each other and they each represent an alkylene group containing 1 to 30 carbon atoms or a phenylene group; and R 1  to R 4  may be identical to or different from each other and they each represent an alkyl group containing 1 to 30 carbon atoms, a phenyl group, or a phenoxy group, 
       
       
         
           
           
               
               
           
         
         wherein in the formula (8), a, b, c, and d are each an integer number of 1 or higher and satisfy the relations of a+b=6 to 17, and c+d=8 to 19, and each broken line represents either a carbon-carbon single bond or a carbon-carbon double bond, 
       
       
         
           
           
               
               
           
         
         wherein in the formula (9), e, f, g, and h are each an integer number of 1 or higher and satisfy the relations of e+f=5 to 16, and g+h=8 to 19, and each broken line represents either a carbon-carbon single bond or a carbon-carbon double bond. 
       
     
     
         5 . A thermosetting resin composition as set forth in  claim 1 , further comprising an epoxy resin (D) and a curing accelerator (E). 
     
     
         6 . A thermosetting resin composition as set forth in  claim 1 , wherein the polyimide resin (A1) and the polyimide resin (A2) each have an imide group equivalent of 350 or more and 1,000 or less. 
     
     
         7 . A thermosetting resin composition as set forth in  claim 1 , wherein the polyimide resin (A1) and the polyimide resin (A2) each contain a diamine residue that has a structure as represented by the formula (3), 
       
         
           
           
               
               
           
         
         wherein in the formula (3), R 7  and R 8  may be identical to or different from each other and they each represent an alkyl group containing 1 to 30 carbon atoms, an alkoxy group, a fluoroalkyl group, a phenyl group, or a phenoxy group. 
       
     
     
         8 . A thermosetting resin composition as set forth in  claim 1 , wherein the polyimide resin (A1) and the polyimide resin (A2) each have a glass transition temperature (Tg) of 100° C. or more and 200° C. or less. 
     
     
         9 . A thermosetting resin composition as set forth in  claim 1 , wherein the phenylene ether resin (B) accounts for 5 wt % or more and 50 wt % or less relative to 100 wt % of the thermosetting resin composition. 
     
     
         10 . A thermosetting resin composition as set forth in  claim 1 , further comprising a silane coupling agent (F) as represented by the formula (12), 
       
         
           
           
               
               
           
         
         wherein in the formula (12), X is an aliphatic or aromatic divalent hydrocarbon group containing 1 to 30 carbon atoms or a single bond; the R 13  groups may be identical to or different from each other and are each a halogen atom, an alkyl group containing 1 to 6 carbon atoms, an alkoxy group containing 1 to 6 carbon atoms, a phenyl group, a hydroxyl group, or a phenoxy group; i is an integer number of 1 to 3, and at least one of the plurality of R 13  groups is a halogen atom or an alkoxy group containing 1 to 6 carbon atoms. 
       
     
     
         11 . A thermosetting resin composition as set forth in  claim 1 , wherein the maleimide resin (C) contains polymaleimide resin molecules each having N maleimide groups (each N is an integer number and the average of N's is larger than 2 and smaller than 30). 
     
     
         12 . A thermosetting resin sheet comprising a support and a thermosetting resin composition as set forth in  claim 1  in the form of a layer in a non-heat-cured state laid thereon. 
     
     
         13 . A cured film produced by curing a thermosetting resin composition as set forth in  claim 1 . 
     
     
         14 . An electronic component comprising a cured film as set forth in  claim 13 . 
     
     
         15 . An electronic component comprising an antenna element having at least one antenna wiring layer and a cured film as set forth in  claim 13 , wherein:
 the antenna wiring layer contains at least one or more selected from the group consisting of meander type loop antenna, coil type loop antenna, meander type monopole antenna, meander type dipole antenna, and microstrip antenna; each antenna part in the antenna wiring layer has an exclusive area of 1,000 mm 2  or less; and the cured film is an insulation film for insulation between the ground and the antenna wiring layer.   
     
     
         16 . An electronic component comprising a semiconductor package containing at least a semiconductor element, a redistribution layer, a molding resin layer, and an antenna wiring layer, wherein:
 the insulating layer in the redistribution layer and/or the molding resin layer contain a cured film as set forth in  claim 13 , and the molding resin layer is located between the ground and the antenna wiring layer.   
     
     
         17 . An electronic component comprising an antenna element containing a stack of an antenna wiring layer and a cured film as set forth in  claim 13 , wherein:
 the antenna wiring layer has a height of 50 to 200 μm and the cured film has a thickness of 80 to 300 μm.   
     
     
         18 . An electronic device comprising an electronic component as set forth in  claim 14 .